Article · 10 min read

Making your first startup ops hire: what founders should look for

Charles Cook · PostHog Free Beginner

Written by PostHog's operations lead, this is the sharpest piece on hiring for judgment over resume. Its core claim, attributes far outweigh technical expertise, maps exactly to our answer: your first ops person will hold admin access to your banking, passwords, and infra, so trust, unflappability, and extreme optimism matter more than a shiny CV. It even hands you interview questions and antipatterns for each trait.

  • Ops is a purely defensive role early on: up to roughly 50 people you are putting out fires, not building systems for hyperscale, so hire someone who stays calm when blamed.
  • This hire gets top-level access to banking, passwords, and infrastructure, so if you would not trust them with that, keep looking.
  • Screen for optimism and dependability with real questions, not for pedigree; a great generalist beats a specialist who cannot roll up their sleeves.
Open on posthog.com ↗

It answers 2 questions

  1. When should I hire my first operations or 'chief of staff' person, and what should they own?
  2. When and how do I make my first non-engineering hire (ops, marketing, or a founder's associate)?

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